(([(3-NITROPHENYL)AMINO]CARBONYL)AMINO)ACETIC ACID synthesis

Yield:67513-14-8 88%

Reaction Conditions:

Stage #1: glycinewith potassium hydroxide in water at 10;
Stage #2: isocyanic acid (3-nitro-phenyl) ester in water;
Stage #3: with hydrogenchloride in 1,4-dioxane;water;

Steps:

a

a. Preparation of N-{[(3-Nitrophenyl)amino]carbonyl}glycine; Potassium hydroxide (10.2 g, 0.154 mol) and glycine (11.25 g, 0.15 mol) were dissolved in water and cooled to 10⁰C. To this was added 3-nitrophenyl isocyanate (25.0 g, 0.15 mol) over 30 mins. The reaction mixture was stirred overnight. Water (80 mL) was added and the reaction mixture was filtered through Celite and the filtrate acidified with 2M HCI. The product was filtered off and washed with water, then dried to give 31.5 g (88%) of Λ/-{[(3-nitrophenyl)amino]carbonyl}glycine: solid; mp 217-218⁰C, R_f 0.40 (EtOAc/MeOH 3:1).

References:

WO2007/18941,2007,A2 Location in patent:Page/Page column 69-70